Wittig reaction

[4] For lithium-free Wittig reactions, studies support a concerted formation of the oxaphosphetane without intervention of a betaine.

In particular, phosphonium ylides 1 react with carbonyl compounds 2 via a [2+2] cycloaddition that is sometimes described as having [π2s+π2a] topology to directly form the oxaphosphetanes 4a and 4b.

Under lithium-free conditions, the stereochemistry of the product 5 is due to the kinetically controlled addition of the ylide 1 to the carbonyl 2.

B. Reitz identified the issue about equilibration of Wittig intermediates and termed the process "stereochemical drift".

[9][10] E. Vedejs has put forth a theory to explain the stereoselectivity of stabilized and unstabilized Wittig reactions.

[12] The Wittig reagents generally tolerate carbonyl compounds containing several kinds of functional groups such as OH, OR, nitroarenes, epoxides, and sometimes esters and amides.

In a so-called tandem oxidation-Wittig process the aldehyde is formed in situ by oxidation of the corresponding alcohol.

[15] For the reaction with aldehydes, the double bond geometry is readily predicted based on the nature of the ylide.

Wittig Reaction
The mechanism of the Wittig reaction
The mechanism of the Wittig reaction
The Schlosser variant of the Wittig reaction
The Schlosser variant of the Wittig reaction
An example of the Schlosser variant of the Wittig reaction
An example of the Schlosser variant of the Wittig reaction
An example of the use of the Wittig reaction in synthesis, making leukotriene A methyl ester
An example of the use of the Wittig reaction in synthesis, making leukotriene A methyl ester